Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
  • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
  • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
  • C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D521/00—Heterocyclic compounds containing unspecified hetero rings
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
  • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
  • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
  • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
  • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
  • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
  • C07D239/32—One oxygen, sulfur or nitrogen atom
  • C07D239/42—One nitrogen atom

Definitions

• a very particularly preferred group are those compounds of the formula (I) in which
• a further very particularly preferred group are those compounds of the formula (I) in which
• n 3 or 4
• n 3 or 4
• the invention furthermore preferably provides sodium, potassium, magnesium, calcium, ammonium, C 1 -C 4 -alkylammonium, di-(C 1 -C 4 -alkyl)ammonium, tri-(C 1 -C 4 -alkyl)ammonium, tetra-(C 1 -C 4 -alkyl)ammonium, tri-(C 1 -C 4 -alkyl)sulfonium, C 5 - or C 6 -cycloalkylammonium and di-(C 1 -C 2 -alkyl)benzylammonium salts of compounds of the formula (I), in which n, A, R 1 , R 2 , R 3 and R 4 have the meanings given above as being preferred.
• radical definitions listed above apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
• alkyl or alkenyl are in each case straight-chain or branched as far as this is possible—including in combination with heteroatoms, such as in alkoxy.
• Optionally substituted radicals may be mono- or polysubstituted, where in the case of polysubstitution the substituents may be identical or different.
• novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) have interesting biological properties. In particular, they have strong herbicidal and fungicidal activity.
• novel substituted fluoroalkoxyphenylsulfonylureas of the general formula (I) can also be obtained as shown schematically below:
• the formula (II) provides a general definition of the aminoazines to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I).
• A, R 1 and R 2 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for A, R 1 and R 2 ;
• Z preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.
• the starting materials of the general formula (II) are known and/or can be prepared by processes known per se (cf. DE-A-19 501 174, U.S. Pat. No. 4,690,707).
• the formula (III) provides a general definition of the fluoroalkoxybenzenesulfonamides further to be used as starting materials in the process according to the invention for preparing compounds of the general formula (I).
• n and R 4 preferably or in particular have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred or as being particularly preferred for n and R 4 .
• starting materials of the general formula (III) are known by disclosure in the form of a generic formula (cf. WO 97/03056). However, the starting materials of the formula (III) are a novel selection from among the prior-art compounds and therefore also form part of the subject matter of the present application. As a preferred group of the starting materials of the formula (III) according to the invention, mention may be made of those compounds in which n and R 4 do not simultaneously represent 2 and unsubstituted alkyl, respectively.
• alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides such as, for example, sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basic organic nitrogen compounds, such as, for example, trimethylamine, triethyl
• tetrabutylammonium bromide tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyltrioctylammonium chloride, hexadecyltrimethylammonium chloride, hexadecyltrimethylammonium bromide, benzyltrimethylammonium chloride, benzyltriethylammonium chloride, benzyltrimethylammonium hydroxide, benzyltriethylammonium hydroxide, benzyltributylammonium chloride, benzyltributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributylhexadecylphosphonium bromide, butyltriphenylphosphonium chloride, ethyl
• the process according to the invention for preparing the compounds of the general formula (I) is preferably carried out using one or more diluents.
• Suitable diluents for carrying out the process according to the invention are, in addition to water, especially inert organic solvents.
• reaction temperatures can be varied within a relatively wide range.
• the process is carried out at temperatures between 0° C. and 150° C., preferably between 10° C. and 120° C.
• the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use a relatively large excess of one of the components.
• the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred at the required temperature for a number of hours. Work-up is carried out by customary methods (cf. the Preparation Examples).
• salts may be prepared from the compounds of the general formula (I) according to the invention.
• Such salts are obtained in a simple manner by customary methods for forming salts, for example by dissolving or dispersing a compound of the formula (I in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and adding a suitable base, such as, for example, sodium hydroxide.
• a suitable solvent such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene
• a suitable base such as, for example, sodium hydroxide.
• the salts can then—if appropriate after prolonged stirring—be isolated by concentration or by filtration with suction (cf. the Preparation Examples).
• the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. Weeds in the broadest sense are understood to mean all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the active compounds according to the invention can be used, for example, in connection with the following plants:
• the active compounds according to the invention are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and rail tracks, and on paths and areas with and without trees.
• the active compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, decorative tree plantations, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, turf and pastureland, and for the selective control of weeds in annual crops.
• the compounds of the formula (I) according to the invention have strong herbicidal activity and a broad activity spectrum when used on the soil and on above-ground parts of plants. To a certain extent they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre-emergence and by the post-emergence method.
• the treatment according to the invention of the plants and plant parts with the active compounds is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space by the customary treatment methods, for example by immersion, spraying, evaporation, fogging, scattering, painting on and, in the case of propagation material, in particular in the case of seeds, also by applying one or more coats.
• formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers.
• extenders that is, liquid solvents and/or solid carriers
• surfactants that is, emulsifiers and/or dispersants, and/or foam formers.
• Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations generally comprise between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used as mixtures with known herbicides and/or substances which improve the compatibility with crop plants (“safeners”), finished formulations or tank mixes being possible. Also possible are mixtures with weed-killers comprising one or more known herbicides and a safener.
• Possible components for the mixtures are known herbicides, for example
• a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, is also possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in a customary manner, for example by watering, spraying, atomizing or broadcasting.
• the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
• the amount of active compound used can vary within a relatively wide range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
• Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the preparation of active compounds such that the particular amount of active compound desired is applied per unit area.
• the concentration of active compound in the spray liquor is chosen such that the particular amount of active compound desired is applied in 1000 liters of water per hectare.
• the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 14, 15, 17, 20, 21, 24, 25 and 26 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, wheat and soya.
• Test plants of a height of 5-15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area.
• the concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 l of water/ha.
• the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 12, 13, 14, 15, 17, 18, 20, 21, 22, 24, 25 and 26 exhibit very strong activity against weeds, and some of them are tolerated well by crop plants, such as, for example, corn, wheat and sugar beet.
• active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
• Evaluation is carried out 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no infection is observed.
• the compounds of Preparation Example 1, 24, 25 and 26 exhibit, at an application rate of 100 g/ha, an efficacy of 100% against mildew of apples ( Podosphaera leucotricha ).

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• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• General Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Wood Science & Technology (AREA)
• Dentistry (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Pharmacology & Pharmacy (AREA)
• Veterinary Medicine (AREA)
• Oncology (AREA)
• Animal Behavior & Ethology (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Communicable Diseases (AREA)
• Public Health (AREA)
• Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
• General Chemical & Material Sciences (AREA)
• Medicinal Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 2001
  • 2001-03-12 DE DE10111649A patent/DE10111649A1/de not_active Withdrawn
• 2002
  • 2002-02-22 AR ARP020100633A patent/AR035434A1/es unknown
  • 2002-02-27 MX MXPA03008139A patent/MXPA03008139A/es active IP Right Grant
  • 2002-02-27 BR BR0208019-2A patent/BR0208019A/pt not_active Application Discontinuation
  • 2002-02-27 CN CNB028064119A patent/CN1229355C/zh not_active Expired - Fee Related
  • 2002-02-27 AT AT02719937T patent/ATE392418T1/de not_active IP Right Cessation
  • 2002-02-27 US US10/469,721 patent/US7723267B2/en not_active Expired - Fee Related
  • 2002-02-27 DE DE50212108T patent/DE50212108D1/de not_active Expired - Lifetime
  • 2002-02-27 KR KR10-2003-7010712A patent/KR20030084929A/ko not_active Abandoned
  • 2002-02-27 ES ES02719937T patent/ES2302803T3/es not_active Expired - Lifetime
  • 2002-02-27 EP EP02719937A patent/EP1373228B1/fr not_active Expired - Lifetime
  • 2002-02-27 CA CA2440280A patent/CA2440280C/fr not_active Expired - Fee Related
  • 2002-02-27 JP JP2002571476A patent/JP2004525129A/ja active Pending
  • 2002-02-27 AU AU2002251024A patent/AU2002251024B2/en not_active Ceased
  • 2002-02-27 WO PCT/EP2002/002064 patent/WO2002072560A1/fr not_active Ceased
  • 2002-02-27 PL PL02362643A patent/PL362643A1/xx unknown
  • 2002-02-27 DK DK02719937T patent/DK1373228T3/da active
• 2007
  • 2007-09-05 US US11/899,364 patent/US20080076667A1/en not_active Abandoned
• 2010
  • 2010-07-16 US US12/837,747 patent/US20100285963A1/en not_active Abandoned

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